Citric Acid → HCID 58336831, compound

HRID 2358985Notes

Reaction equation

HRID 2358985 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Mg]Cl)(C)C.[CH3:14][O:15][CH2:16][C:17](N(C)C)=[O:18].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[OH-].[Na+].[Na+].[Cl-]>C1COCC1.C(OCC)(=O)C>[Br:8][C:4]1[N:3]=[C:2]([C:17](=[O:18])[CH2:16][O:15][CH3:14])[CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 6

HCID 311Citric AcidHCID 5234Sodium ChlorideHCID 122742,6-DibromopyridineHCID 14798Sodium HydroxideHCID 11126230Acetamide, 2-methoxy-N,N-dimethyl-HCID 178418918HCID 178418918, compound

Product 1

HCID 58336831HCID 58336831, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

14.5 g (61.2 mmol) of 2,6-dibrompyridine were dissolved in about 50 ml of THF, and 35 ml of 2 M isopropylmagnesium chloride (corresponds to 70 mmol) were added under argon. The temperature of the mixture increased. The mixture was stirred at room temperature for another 1.5 h and at 30° C. for 2 h and then cooled in a CO2/EtOH bath, and a solution of 8 g (68.2 mmol) of 2-methoxy-N,N-dimethylacetamide in THF was added, the thickened reaction material was diluted with more THF and allowed to thaw, ethyl acetate, aq. citric acid, dil. aqueous sodium hydroxide solution to pH=6, aq. NaCl were added, the aqueous phase was extracted three times with ethyl acetate and the combined organic phases were dried with MgSO4 and concentrated by evaporation. The residue was distilled under reduced pressure in a kugelrohr and the distillate was recrystallized from a little benzotrifluoride.

Workup

  1. temperatureThe temperature of the mixture increased
  2. temperaturecooled in a CO2/EtOH bath
  3. additionwere added
  4. extractionthe aqueous phase was extracted three times with ethyl acetate
  5. dry with materialthe combined organic phases were dried with MgSO4
  6. concentrationconcentrated by evaporation
  7. distillationThe residue was distilled under reduced pressure in a kugelrohr
  8. customthe distillate was recrystallized from a little benzotrifluoride

Sources & evidence

ORD record
ord-f8f987e797fe446695ab0f22ac4ceddf
Source dataset
uspto-grants-2014_04
Patent number
US08685964B2

Reaction notes

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